GB1099691A - Heterocyclic carbonates and thiocarbamates and their use as insecticides and nematocides - Google Patents
Heterocyclic carbonates and thiocarbamates and their use as insecticides and nematocidesInfo
- Publication number
- GB1099691A GB1099691A GB2831/65A GB283165A GB1099691A GB 1099691 A GB1099691 A GB 1099691A GB 2831/65 A GB2831/65 A GB 2831/65A GB 283165 A GB283165 A GB 283165A GB 1099691 A GB1099691 A GB 1099691A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- hydrogen
- methyl
- prepared
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Heterocyclic carbonates Chemical class 0.000 title abstract 4
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 title abstract 2
- 239000002917 insecticide Substances 0.000 title 1
- 230000001069 nematicidal effect Effects 0.000 title 1
- 239000005645 nematicide Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- WDZLZKSUBSXWID-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-2-ol Chemical class C1=CC=C2OC(O)CC2=C1 WDZLZKSUBSXWID-UHFFFAOYSA-N 0.000 abstract 3
- SSUFJVXUMQIJAX-UHFFFAOYSA-N 1-benzofuran-2-yl carbamate Chemical class C1=CC=C2OC(OC(=O)N)=CC2=C1 SSUFJVXUMQIJAX-UHFFFAOYSA-N 0.000 abstract 2
- WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 230000000911 decarboxylating effect Effects 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- WMLQSABJYOWERL-UHFFFAOYSA-N 1-benzofuran-2-yl carbonochloridate Chemical compound C1=CC=C2OC(OC(=O)Cl)=CC2=C1 WMLQSABJYOWERL-UHFFFAOYSA-N 0.000 abstract 1
- UHXBMSNEECJPSX-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1OCC2 UHXBMSNEECJPSX-UHFFFAOYSA-N 0.000 abstract 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 abstract 1
- RFYXCNWJGXDJIV-UHFFFAOYSA-N 3-hydroxy-1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2C(O)=C(C(=O)O)OC2=C1 RFYXCNWJGXDJIV-UHFFFAOYSA-N 0.000 abstract 1
- PYXLGMKGMXVZRX-UHFFFAOYSA-N 4-hydroxy-2,2-dimethyl-3h-1-benzofuran-5-carboxylic acid Chemical compound C1=CC(C(O)=O)=C(O)C2=C1OC(C)(C)C2 PYXLGMKGMXVZRX-UHFFFAOYSA-N 0.000 abstract 1
- ZWCOUCOUSVSBAW-UHFFFAOYSA-N 5-chloro-2,2-dimethyl-3h-1-benzofuran-7-ol Chemical class ClC1=CC(O)=C2OC(C)(C)CC2=C1 ZWCOUCOUSVSBAW-UHFFFAOYSA-N 0.000 abstract 1
- ADDCNCINMAVAMI-UHFFFAOYSA-N 7-hydroxy-1-benzofuran-2-carboxylic acid Chemical compound C1=CC(O)=C2OC(C(=O)O)=CC2=C1 ADDCNCINMAVAMI-UHFFFAOYSA-N 0.000 abstract 1
- UOCNTRAAJNWDND-UHFFFAOYSA-N 7-methoxy-1-benzofuran-2-carboxylic acid Chemical compound COC1=CC=CC2=C1OC(C(O)=O)=C2 UOCNTRAAJNWDND-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- 239000004606 Fillers/Extenders Substances 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 abstract 1
- 229960001860 salicylate Drugs 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004563 wettable powder Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US339612A US3474171A (en) | 1964-01-23 | 1964-01-23 | 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-n-methylcarbamate |
| US403324A US3474170A (en) | 1964-01-23 | 1964-10-12 | Pesticidal carbamates of dihydrobenzofuranols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1099691A true GB1099691A (en) | 1968-01-17 |
Family
ID=26991711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2831/65A Expired GB1099691A (en) | 1964-01-23 | 1965-01-22 | Heterocyclic carbonates and thiocarbamates and their use as insecticides and nematocides |
Country Status (13)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007719A3 (en) * | 1978-07-29 | 1980-05-14 | Fbc Limited | Cyanbenzofuran derivatives, processes for their preparation and their use in herbicidal compositions; cyanobenzene, benzodioxepine, benzodioxaphosphepine and benzodioxathiepine derivatives |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419579A (en) * | 1966-02-23 | 1968-12-31 | Fmc Corp | Synthesis of 2,3-dihydro-2,2-dimethyl-7-benzofuranol |
| US3876667A (en) * | 1971-11-08 | 1975-04-08 | Ici Australia Ltd | Synthesis of 2,3-dihydro-2,2-dimethyl-7-benzofuranyl-n-methyl carbamate starting from ortho-isopropylphenol and methallyl halide |
| US4215115A (en) * | 1976-11-24 | 1980-07-29 | Fmc Corporation | Nematicidal phosphorodithioate |
| US4201786A (en) * | 1977-05-27 | 1980-05-06 | Union Carbide Corporation | Water soluble pesticidal quaternary ammonium salt compounds |
| US4118400A (en) * | 1977-09-22 | 1978-10-03 | Fmc Corporation | Process for preparing 2,3-dihydro-7-benzofuranols and benzodioxole intermediate therefor |
| IL58661A (en) * | 1978-11-30 | 1983-11-30 | Philagro Sa | Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| FR2461708A1 (fr) * | 1979-07-18 | 1981-02-06 | Rhone Poulenc Agrochimie | Preparation de dihydrodimethylhydroxy-7 benzofurane |
| DE2932458A1 (de) * | 1979-08-10 | 1981-02-26 | Bayer Ag | Herstellung von monoalkylethern von hydroxyphenolen und deren umwandlung zu hydroxycumaranen |
| FR2470768A1 (fr) * | 1979-12-07 | 1981-06-12 | Rhone Poulenc Agrochimie | Procede de preparation de derives de benzofuranne |
| US4465868A (en) * | 1981-07-17 | 1984-08-14 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing o-methallyloxyphenol |
| US4451662A (en) * | 1981-09-01 | 1984-05-29 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| US4419350A (en) * | 1981-11-05 | 1983-12-06 | Stauffer Chemical Company | Carbofuran compositions for problem soils |
| US4380654A (en) * | 1982-02-18 | 1983-04-19 | Fmc Corporation | Process for preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| HU191184B (en) * | 1982-07-09 | 1987-01-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Stabilized herbicide suspension |
| IT1199987B (it) * | 1983-02-04 | 1989-01-05 | Brichima Spa | Processo per la produzione di derivati benzofuranici |
| US4639536A (en) * | 1984-08-30 | 1987-01-27 | Union Carbide Corporation | Intermediate, its synthesis, and its use in a process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| HU207197B (en) * | 1987-07-16 | 1993-03-29 | Chinoin Gyogyszer Es Vegyeszet | Plant protecting solution and aquous suspension containing water insoluble active component |
| US4982012A (en) * | 1987-12-18 | 1991-01-01 | Fmc Corporation | Two phase process for preparing 2-methallyloxyphenol from catechol |
| US4851587A (en) * | 1988-05-31 | 1989-07-25 | Fmc Corporation | Single solvent process for preparing 2-methallyloxy-phenol from catechol |
| US4987233A (en) * | 1988-06-15 | 1991-01-22 | Eli Lilly And Company | Process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives |
| JP2006525336A (ja) * | 2003-04-30 | 2006-11-09 | エフ エム シー コーポレーション | フェニル置換した環状誘導体 |
| DE102007045955A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2410847A1 (de) | 2009-03-25 | 2012-02-01 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden eigenschaften |
| AU2011340258C1 (en) | 2010-12-06 | 2016-10-20 | Autifony Therapeutics Limited | Hydantoin derivatives useful as Kv3 inhibitors |
| CN104496973B (zh) * | 2015-01-23 | 2016-11-30 | 邵阳学院 | 呋喃酚丙烯酮衍生物作为杀虫剂的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2362479A (en) * | 1943-08-04 | 1944-11-14 | Goodrich Co B F | Antioxidant for rubber |
-
1964
- 1964-10-12 US US403324A patent/US3474170A/en not_active Expired - Lifetime
-
1965
- 1965-01-03 IL IL22718A patent/IL22718A/en unknown
- 1965-01-12 BE BE658194A patent/BE658194A/xx unknown
- 1965-01-12 NL NL656500340A patent/NL148605B/xx not_active IP Right Cessation
- 1965-01-13 FR FR1836A patent/FR1436588A/fr not_active Expired
- 1965-01-20 AT AT42365A patent/AT276851B/de not_active IP Right Cessation
- 1965-01-20 CH CH1286167A patent/CH478525A/de not_active IP Right Cessation
- 1965-01-22 LU LU47823A patent/LU47823A1/xx unknown
- 1965-01-22 SE SE6292/67A patent/SE346205B/xx unknown
- 1965-01-22 GB GB2831/65A patent/GB1099691A/en not_active Expired
- 1965-01-22 ES ES0308421A patent/ES308421A1/es not_active Expired
- 1965-01-22 DE DE1965F0049578 patent/DE1542879B2/de active Granted
- 1965-01-22 DK DK34765AA patent/DK117775B/da unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007719A3 (en) * | 1978-07-29 | 1980-05-14 | Fbc Limited | Cyanbenzofuran derivatives, processes for their preparation and their use in herbicidal compositions; cyanobenzene, benzodioxepine, benzodioxaphosphepine and benzodioxathiepine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| BE658194A (enrdf_load_stackoverflow) | 1965-07-12 |
| US3474170A (en) | 1969-10-21 |
| FR1436588A (fr) | 1966-04-29 |
| NL148605B (nl) | 1976-02-16 |
| SE346205B (enrdf_load_stackoverflow) | 1972-07-03 |
| DE1542879A1 (de) | 1970-06-04 |
| DK117775B (da) | 1970-06-01 |
| NL6500340A (enrdf_load_stackoverflow) | 1965-07-26 |
| DE1542879B2 (de) | 1977-04-07 |
| LU47823A1 (enrdf_load_stackoverflow) | 1965-03-22 |
| CH478525A (de) | 1969-09-30 |
| AT276851B (de) | 1969-12-10 |
| IL22718A (en) | 1970-01-29 |
| ES308421A1 (es) | 1965-05-16 |
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